JP5538725B2 - 新規糖脂質アジュバント組成物 - Google Patents

新規糖脂質アジュバント組成物 Download PDF

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Publication number: JP5538725B2
Authority: JP; Japan
Prior art keywords: acid; glycolipid; pka; formula; weak
Prior art date: 2006-01-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

JP2008551904A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009524638A (ja

Inventor

ジョセフドミノウスキポール

マナーマンナンラマサミー

メディラッタサンギタ

Original Assignee

ゾエティス・ピー・エルエルシー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-01-26

Filing date

2007-01-15

Publication date

2014-07-02

2007-01-15 Application filed by ゾエティス・ピー・エルエルシー filed Critical ゾエティス・ピー・エルエルシー

2009-07-02 Publication of JP2009524638A publication Critical patent/JP2009524638A/ja

2014-07-02 Application granted granted Critical

2014-07-02 Publication of JP5538725B2 publication Critical patent/JP5538725B2/ja

Status Active legal-status Critical Current

2027-01-15 Anticipated expiration legal-status Critical

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229930186217 Glycolipid Natural products 0.000 title claims description 170
HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 title claims description 162
239000000203 mixture Substances 0.000 title claims description 43
239000002671 adjuvant Substances 0.000 title description 110
239000000243 solution Substances 0.000 claims description 116
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 97
-1 L-α-aminobutyl Chemical group 0.000 claims description 82
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
239000002253 acid Substances 0.000 claims description 64
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 62
239000000427 antigen Substances 0.000 claims description 41
102000036639 antigens Human genes 0.000 claims description 41
108091007433 antigens Proteins 0.000 claims description 41
241000700605 Viruses Species 0.000 claims description 38
239000011780 sodium chloride Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 27
150000003839 salts Chemical group 0.000 claims description 27
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
239000000872 buffer Substances 0.000 claims description 18
239000002736 nonionic surfactant Substances 0.000 claims description 18
150000007513 acids Chemical class 0.000 claims description 17
229920001214 Polysorbate 60 Polymers 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
241000283690 Bos taurus Species 0.000 claims description 11
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 10
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
239000007983 Tris buffer Substances 0.000 claims description 9
239000008363 phosphate buffer Substances 0.000 claims description 9
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
229920001213 Polysorbate 20 Polymers 0.000 claims description 8
239000004147 Sorbitan trioleate Substances 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 8
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
235000019337 sorbitan trioleate Nutrition 0.000 claims description 8
229960000391 sorbitan trioleate Drugs 0.000 claims description 8
229960005486 vaccine Drugs 0.000 claims description 8
125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 7
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 6
125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims description 6
125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 claims description 6
125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims description 6
125000000415 L-cysteinyl group Chemical group O=C([*])[C@@](N([H])[H])([H])C([H])([H])S[H] 0.000 claims description 6
125000003338 L-glutaminyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims description 6
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 claims description 6
125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims description 6
125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 6
125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 claims description 6
125000000769 L-threonyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](O[H])(C([H])([H])[H])[H] 0.000 claims description 6
125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 6
125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims description 6
ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical compound OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 claims description 6
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 6
229920000053 polysorbate 80 Polymers 0.000 claims description 6
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
239000001530 fumaric acid Substances 0.000 claims description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
239000011976 maleic acid Substances 0.000 claims description 5
239000000463 material Substances 0.000 claims description 5
239000011664 nicotinic acid Substances 0.000 claims description 5
235000001968 nicotinic acid Nutrition 0.000 claims description 5
229960003512 nicotinic acid Drugs 0.000 claims description 5
229940107700 pyruvic acid Drugs 0.000 claims description 5
239000001384 succinic acid Substances 0.000 claims description 5
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 4
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical group CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
239000004471 Glycine Substances 0.000 claims description 4
208000002606 Paramyxoviridae Infections Diseases 0.000 claims description 4
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims description 4
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 4
IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
230000002209 hydrophobic effect Effects 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
229960004838 phosphoric acid Drugs 0.000 claims description 4
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 4
229940035044 sorbitan monolaurate Drugs 0.000 claims description 4
239000001593 sorbitan monooleate Substances 0.000 claims description 4
235000011069 sorbitan monooleate Nutrition 0.000 claims description 4
229940035049 sorbitan monooleate Drugs 0.000 claims description 4
235000011078 sorbitan tristearate Nutrition 0.000 claims description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
UMTBGMXFTSIKBH-UHFFFAOYSA-N 1-amino-3-hydroxypropane-2-sulfonic acid Chemical compound NCC(CO)S(O)(=O)=O UMTBGMXFTSIKBH-UHFFFAOYSA-N 0.000 claims description 3
SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 3
239000007995 HEPES buffer Substances 0.000 claims description 3
239000007993 MOPS buffer Substances 0.000 claims description 3
HVUMOYIDDBPOLL-IIZJTUPISA-N [2-[(2r,3s,4r)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O HVUMOYIDDBPOLL-IIZJTUPISA-N 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
229940098895 maleic acid Drugs 0.000 claims description 3
239000001488 sodium phosphate Substances 0.000 claims description 3
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235000011008 sodium phosphates Nutrition 0.000 claims description 3
235000011071 sorbitan monopalmitate Nutrition 0.000 claims description 3
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239000001587 sorbitan monostearate Substances 0.000 claims description 3
235000011076 sorbitan monostearate Nutrition 0.000 claims description 3
229940035048 sorbitan monostearate Drugs 0.000 claims description 3
239000001589 sorbitan tristearate Substances 0.000 claims description 3
229960004129 sorbitan tristearate Drugs 0.000 claims description 3
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 3
241001529453 unidentified herpesvirus Species 0.000 claims description 3
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
235000010323 ascorbic acid Nutrition 0.000 claims description 2
229960005070 ascorbic acid Drugs 0.000 claims description 2
239000011668 ascorbic acid Substances 0.000 claims description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 claims description 2
239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
235000019441 ethanol Nutrition 0.000 claims 11
239000012062 aqueous buffer Substances 0.000 claims 3
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims 2
230000004083 survival effect Effects 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
229910000160 potassium phosphate Inorganic materials 0.000 claims 1
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
150000001875 compounds Chemical class 0.000 description 38
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238000004220 aggregation Methods 0.000 description 29
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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150000002341 glycosylamines Chemical class 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
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239000003085 diluting agent Substances 0.000 description 10
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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EP (2)	EP1991266B1 (me)
JP (1)	JP5538725B2 (me)
KR (2)	KR101202553B1 (me)
AR (1)	AR059192A1 (me)
AU (1)	AU2007209104B2 (me)
BR (1)	BRPI0706709B8 (me)
CA (1)	CA2634888C (me)
CY (1)	CY1114310T1 (me)
DK (1)	DK1991266T3 (me)
ES (1)	ES2425576T3 (me)
HK (1)	HK1128078A1 (me)
ME (3)	ME01545B (me)
NO (1)	NO341463B1 (me)
NZ (1)	NZ569375A (me)
PL (1)	PL1991266T3 (me)
PT (1)	PT1991266E (me)
RS (2)	RS52930B (me)
RU (1)	RU2392965C2 (me)
TW (1)	TWI372631B (me)
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WO2014141127A1 (en) *	2013-03-15	2014-09-18	Glaxosmithkline Biologicals S.A.	Composition containing buffered aminoalkyl glucosaminide phosphate derivatives and its use for enhancing an immune response
WO2015042369A2 (en)	2013-09-19	2015-03-26	Zoetis Llc	Oil-based adjuvants
CA2932878C (en)	2013-11-26	2020-11-03	Zoetis Services Llc	Compositions for induction of immune response
PL3244920T3 (pl)	2015-01-16	2023-09-25	Zoetis Services Llc	Szczepionka przeciw pryszczycy
ES2878475T3 (es) *	2015-07-20	2021-11-18	Zoetis Services Llc	Composiciones adyuvantes liposomales
GB201703529D0 (en)	2017-03-06	2017-04-19	Cambridge Entpr Ltd	Vaccine composition
CN110713520B (zh) *	2019-11-06	2021-01-01	中国石油天然气股份有限公司	油酰基氨基酸-γ-L-谷氨酰-L-半胱氨酰-甘氨酸多肽及其制备与应用
TW202206098A (zh)	2020-08-11	2022-02-16	美商碩騰服務公司	抗冠狀病毒疫苗
WO2022072431A1 (en)	2020-09-30	2022-04-07	Zoetis Services Llc	Novel pasteurella multocida strains and vaccines having hyac and nanp deletions

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BR0114392A (pt) *	2000-10-02	2003-09-02	Glaxosmithkline Biolog Sa	Formulação de vacina, método para produzir uma formulação de vacina, uso de uma preparação de vacina contra rsv dividido, kit para liberação de uma formulação de vacina intranasal, dispositivo de liberação intranasal, e, método para proteger ou tratar um mamìfero susceptìvel a, ou sofrendo de doença causada por rsv

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Publication number	Publication date
CY1114310T1 (el)	2016-08-31
WO2007085962A2 (en)	2007-08-02
ES2425576T3 (es)	2013-10-16
RU2008129203A (ru)	2010-03-10
EP1991266A2 (en)	2008-11-19
RS52930B (en)	2014-02-28
BRPI0706709A2 (pt)	2011-04-05
AR059192A1 (es)	2008-03-12
ME01545B (me)	2014-04-20
HK1128078A1 (en)	2009-10-16
RU2392965C2 (ru)	2010-06-27
NO20083405L (no)	2008-10-23
PL1991266T3 (pl)	2013-11-29
NZ569375A (en)	2010-05-28
CA2634888A1 (en)	2007-08-02
EP1991266B1 (en)	2013-06-26
JP2009524638A (ja)	2009-07-02
US8460679B2 (en)	2013-06-11
CA2634888C (en)	2016-06-21
TWI372631B (en)	2012-09-21
MEP4508A (en)	2010-06-10
PT1991266E (pt)	2013-08-28
BRPI0706709B1 (pt)	2021-03-23
DK1991266T3 (da)	2013-08-26
BRPI0706709B8 (pt)	2021-05-25
WO2007085962A3 (en)	2007-12-27
US20070196384A1 (en)	2007-08-23
KR101202553B1 (ko)	2012-11-20
AU2007209104B2 (en)	2010-04-08
TW200738268A (en)	2007-10-16
ME00045B (me)	2010-10-10
EP2481423A1 (en)	2012-08-01
AU2007209104A1 (en)	2007-08-02
NO341463B1 (no)	2017-11-20
KR20110140140A (ko)	2011-12-30
RS20080318A (en)	2009-05-06
KR20080080223A (ko)	2008-09-02

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